Hilltop Hideaway • Hot Tub, Views & Nature Trails

Escape to the Berkshires and discover Hilltop Hideaway, a spacious 5-bedroom guesthouse perched atop a scenic hill in Southfield, MA. Nestled on a private 100-acre estate with curated hiking trails, open meadows, and sweeping views of Haystack Mountain, this peaceful retreat blends upscale amenities with unmatched natural beauty.

Unwind in the private hot tub, dine al fresco on the stone patio, or gather around the firepit under starry skies. Inside, enjoy a fully equipped chef’s kitchen, an open-concept great room, and thoughtful comforts throughout. While the property is shared with the owner’s residence, the guesthouse sits apart at the top of the drive with its own dedicated entrance and parking area, offering a private and comfortable stay—perfect for families, friends, or anyone seeking a peaceful getaway.

SLEEPING ARRANGEMENTS:
• Bedroom 1 (Main Level): King bed + en suite bath with walk-in shower
• Bedroom 2 (Second Floor): Queen bed + 2 twin beds + en suite bath (tub/shower)
• Bedroom 3 (Second Floor): Queen bed + en suite bath (tub/shower)
• Bedroom 4 (Second Floor): Full bed
• Bedroom 5 (Lower Level): Queen bed adjacent full bath with jetted tub & steam shower

INDOOR FEATURES:
• Gourmet kitchen with Subzero fridge, Wolf range, soapstone counters & drip coffee maker
• Two prep islands + dining table for 8
• Great room with gas fireplace, streaming TV & game table
• Steam shower and jetted tub
• Private gym with cardio equipment, free weights & yoga swing

OUTDOOR FEATURES:
• Bluestone patio with Adirondack chairs & wood-burning firepit
• Propane grill & outdoor dining table with umbrella
• Secluded hot tub with woodland views

ADDITIONAL INFO:
• Private guest entrance and parking
• High-speed WiFi and streaming capabilities
• Washer/dryer in-unit
• Owners live on-site (separate home) with two friendly, off-leash dogs
• Pet-friendly (max 2 dogs, $100 per pet)
• Cleaning fee: $450
• Extra guest fee: $25/night for more than 8 guests (max occupancy: 12)

Whether you’re exploring mountain trails, soaking in the hot tub, or enjoying game night by the fire, Hilltop Hideaway offers a serene, year-round escape in the heart of the Berkshires. Ideal for wellness weekends, family gatherings, romantic getaways, or friends’ retreats, this all-season sanctuary blends luxury and nature seamlessly—just a short 25 minute drive from Great Barrington, cultural landmarks, and acclaimed farm-to-table dining.